151950-83-3Relevant academic research and scientific papers
Enantioselective copper-catalyzed intramolecular phenolic O-H bond insertion: Synthesis of chiral 2-carboxy dihydrobenzofurans, dihydrobenzopyrans, and tetrahydrobenzooxepines
Song, Xiao-Guang,Zhu, Shou-Fei,Xie, Xiu-Lan,Zhou, Qi-Lin
supporting information, p. 2555 - 2558 (2013/04/10)
Efficient: A copper-catalyzed enantioselective intramolecular insertion of carbenoids into phenolic O-H bonds has been developed. This method can be used for the synthesis of the title compounds in high yields and excellent enantioselectivities under mild and neutral conditions (see scheme). NaBAr F=sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate. Copyright
Intramolecular Enantioselective Palladium-Catalyzed Heck Arylation of Cyclic Enamides
Ripa, Lena,Hallberg, Anders
, p. 595 - 602 (2007/10/03)
Palladium-catalyzed intramolecular cyclization of N-formyl-6--1,2,3,4-tetrahydropyridine (1a) and N-formyl-6--1,2,3,4-tetrahydropyridine (1b) in the presence of AsPh3 resulted in formation of the spiro compounds N-formyl-3,3',4,4'-tetrahydrospiro (2a) and N-formyl-3',4'-dihydrospiro (2b), respectively, and in the presence of PPh3 and TlOAc in the spiro compounds N-formyl-3,4,5',6'-tetrahydrospiro (3a) and N-formyl-5',6'-dihydrospiro (3b), respectively.Cyclization of N-formyl-6-(3-phenyl>propyl)-1,2,3,4-tetrahydropyridine (7) in presence of a chiral (phosphinoaryl)oxazoline ((S)-8) resulted in formation of (R)-3a and (R)-N-formyl-1',3,4,6'-tetrahydrospiro ((R)-6a) in high enantiomeric excesses, 87 percent and >99percent, respectively, and in good yield.The oxazoline ligand (S)-8 furnished higher enantiomeric excesses and improved regioselectivities than (R)-BINAP.
